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Triethylamine → N-(2-methoxy-2-methylpropyl)-6-methyl-2-(methylthio)pyrido[3,4-d]pyrimidin-8-amine

HRID 1480854
Notes
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Reaction equation

HRID 1480854 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[CH:5]=[C:4]([CH3:14])[N:3]=1.[CH3:15][O:16][C:17]([CH3:21])([CH3:20])[CH2:18][NH2:19].C(N(CC)CC)C>CN1C(=O)CCC1.CCOC(C)=O>[CH3:15][O:16][C:17]([CH3:21])([CH3:20])[CH2:18][NH:19][C:2]1[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[CH:5]=[C:4]([CH3:14])[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 117891412-Methoxy-2-methylpropan-1-amineHCID 899960218-Chloro-6-methyl-2-(methylthio)pyrido[3,4-d]pyrimidine

Product 1

HCID 89996204N-(2-methoxy-2-methylpropyl)-6-methyl-2-(methylthio)pyrido[3,4-d]pyrimidin-8-amineYield 61%

Reagents, catalysts & solvents 2

HCID 8857Ethyl Acetate
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 8-chloro-6-methyl-2-(methylthio)pyrido[3,4-d]pyrimidine (Preparation 52, 80 mg, 0.354 mmol) in NMP (7 mL) was added 2-methoxy-2-methylpropan-1-amine (0.086 ml, 0.709 mmol) and triethylamine (0.249 mL, 1.772 mmol). The reaction mixture was heated to 120° C. for 18 hours. The reaction mixture was diluted with EtOAc (30 mL), washed with water (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-50% EtOAc in cyclohexane to afford the title compound (63 mg, 61%).

Workup

  1. washwashed with water (30 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with 0-50% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-a5b01d5798164e9ba9df9a9b89557210
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409907B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes